Water → HCID 18663506, compound

HRID 1957035Notes

Reaction equation

HRID 1957035 reaction equation
C([O:3][C:4](=[O:30])[C@H:5]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][N:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[N:6]([C:8](=[O:17])[C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1)[CH3:7])C.O.[OH-].[Li+].O>CO.O1CCCC1>[CH3:15][C:13]1[CH:14]=[C:9]([CH:10]=[C:11]([CH3:16])[CH:12]=1)[C:8]([N:6]([CH3:7])[C@H:5]([C:4]([OH:30])=[O:3])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][N:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18663507HCID 18663507, compound

Product 1

HCID 18663506HCID 18663506, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester is treated with lithium hydroxide monohydrate (5 mg) in methanol (0.5 ml), tetrahydrofuran (0.25 ml), and water (0.25 ml) for 3 hours at room temperature. The mixture is then partitioned between water and ether, the water phase acidified with 1N hydrochloric acid, and subsequently extracted with ethyl acetate. The ethyl acetate phase is washed with brine, dried, and evaporated to give N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-alanine. NMR (CDCl3, 400 MHz) δ [ppm] 8.48 (s), 8.30 (s), 7.80 (m), 7.43 (m), 7.13 (m), 7.03 (s), 6.94 (s), 6.75 (s), 6.69 (s), 6,54 (s), 6.36 (s), 5.16 (m), 4.65 (m), 3.55 (m), 3.40 (m), 3.25 (m), 3.10 (m), 2.80 (s), 2.26 (s), 2.14 (s).

Workup

  1. customThe mixture is then partitioned between water and ether
  2. extractionsubsequently extracted with ethyl acetate
  3. washThe ethyl acetate phase is washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-f7dc37fcb0f6430d8e8910d43aed093d
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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